136265-10-6

Upstream product

• 459-32-5 4-fluorocinnamic acid 
• 64-17-5 ethanol 
• 459-57-4 4-fluorobenzaldehyde 
• 141-78-6 ethyl acetate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 78795-71-8 C₁₂H₈ClFTe 
• 140-88-5 ethyl acrylate 
• 13565-08-7 4-fluorocinnamoyl chloride 
• 462-06-6 fluorobenzene 
• 74929-23-0 3-(4-fluorophenyl)-2-propynal 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 105-36-2 ethyl bromoacetate 
• 15894-04-9 (4-fluorophenyl)methanethiol 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 7116-38-3 ethyl 3-(4-fluorophenyl)propanoate 
• 116608-92-5 5-(4-Fluoro-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 701-47-3 1-(4-fluorophenyl)propanol 
• 124980-95-6 3-(4-fluorophenyl)prop-2-en-1-ol 
• 1093858-31-1 C₂₆H₂₂F₂N₂O₄ 
• 191668-10-7 ethyl 4-(4-fluorophenyl)-1H-pyrrole-3-carboxylate 
• 124980-95-6 (E)-3-(4-fluorophenyl)-2-propen-1-ol 
• 911301-34-3 ethyl 2-azido-3-(4-fluorophenyl)acrylate 
• 1187248-63-0 C₁₁H₁₁BrFN₃O₂ 

Relevant academic research and scientific papers

Atomically precise palladium nanocluster catalyzed tandem oxidation processes of alcohols and phosphorous ylides: Facile access to α,β-unsaturated esters

The mesoporous silica nanosphere supported palladium nanocluster was synthesized through a simple impregnation method and well characterized. The as prepared catalyst shows excellent catalytic performance in tandem oxidation process (TOP) of alcohol and phosphorous ylide, which provides an efficient access to α,β-unsaturated esters with high yields utilizes 1 atmosphere of molecular oxygen as sole oxidant. This work represents the first example of atomically precise palladium nanocluster catalyzed tandem oxidation process of alcohol and phosphorous ylide and is expected to open new horizons for nanoclusters in the tandem reactions.

Palladium-catalyzed conversion of aldehydes to alkenes in the presence of tri-n-butylphosphine

Palladium-catalyzed conversion of aldehydes to alkenes in the presence of tri-n-butylphosphine is described.

Synthesis and in vitro evaluation of antimycobacterial and cytotoxic activity of new α,β-unsaturated amide, oxazoline and oxazole derivatives from L-serine

The synthesis of 19 compounds derived from L-serine and analogs of p-substituted cinnamic acid is reported. Oxazolines 9 and oxazoles 10 have high antitubercular activity with Minimum Inhibitory Concentration (MIC) of 0.7812–25.0 μg/mL (3.21–100.3 μM), against two strains of Mycobacterium tuberculosis sensitive to first-line drugs Isoniazid (INH), Rifampicin (RIF), Ethambutol (EMB), Pyrazinamide (PZE) (H37Rv) and a clinical isolate resistant to INH, RIF and EMB (G122). The cytotoxic evaluation shows that oxazoles have low activity, finding viability>96% against the VERO cell line. The results show these compounds could be considered as future alternatives for antitubercular treatment.

A One-Pot Synthesis of α,β-Unsaturated Esters From Esters

A convenient method for reductive Horner–Wadsworth–Emmons (HWE) olefination is described. The E-selective HWE homologation of various esters to α,β-unsaturated esters was readily achieved and gave the desired products in good-to-moderate yields under mild conditions. The one-pot reaction proceeds through an in situ generated aldehyde, formed via the partial reduction of an ester with lithium diisobutyl-t-butoxyaluminum hydride. The formation of cyclized metal acetal and subsequent decompose to the aldehyde for the olefination was found to be a crucial step in this C2-carbon homologation protocol.

Quantitative Structure-Property Relationship (QSPR) models for a local quantum descriptor: Investigation of the 4- and 3-substituted-cinnamic acid esterification

In this work, the theoretical description of the 4- and 3-substituted-cinnamic acid esterification with different electron donating and electron withdrawing groups was performed at the B3LYP and M06-2X levels, as a two-step process: the O-protonation and the nucleophile attack by ethanol. In parallel, an experimental work devoted to the synthesis and characterization of the substituted-cinnamate esters has also been performed. In order to quantify the substituents effects, quantitative structure-property relationship (QSPR) models based on the atomic charges, Fukui functions and the Frontier Effective-for-Reaction Molecular Orbitals (FERMO) energies were investigated. In fact, the Fukui functions, f+C and f-O, indicated poor correlations for each individual step, and in contrast with the general literature, the O-protonation step is affected both by the FERMO energies and the O-charges of the carbonyl group. Since the process was shown to not be totally described by either charge- or frontier-orbitals, it is proposed to be frontier-charge-miscere controlled. Moreover, the observed trend for the experimental reaction yields suggests that the electron withdrawing groups favor the reaction and the same was observed for Step 2, which can thus be pointed out as the determining step.

Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites

The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had

Identification of (6S)-cyclopropyl-6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxamines as new HBV capsid assembly modulators

GYH2-18 is a type II HBV CAM with 6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxamine (DPPC) skeleton discovered by Roche INC. A series of GYH2-18 derivatives were designed, synthesized and evaluated for their anti-HBV activity. Two compounds 2f and 3k exhibited excellent anti-HBV activity, low cytotoxicity and accepted oral PK profiles. Chiral separation of 2f and 3k was conducted successfully, and (6S)-cyclopropyl DPPC isomers 2f-1, 2f-3, 3k-1 and 3k-3 were identified to be much more active than the corresponding (6R)-ones. The preliminary structure-activity relationship, particle gel assay and molecular modeling studies were also discussed, which provide useful indications for guiding the further rational design of new (6S)-cyclopropyl DPPC analogues.

Synthesis method of selenium-containing isochroman compound

The invention discloses a synthesis method of a selenium-containing isochroman compound. The synthesis method comprises the following steps: under the protection of nitrogen, adding N-phenylseleno saccharin (NPSSac) into a reactor, then adding dichloromethane to completely dissolve the N-phenylseleno saccharin, adding a 1-[(cinnamoxy) methyl]-3, 4, 5-trimethoxy benzene compound and boron trifluoride diethyl etherate after the N-phenylseleno saccharin is completely dissolved, stirring at 20-60 DEG C for 2-6 hours until the reaction is complete, and after the reaction is finished, quenching, extracting, combining organic phases, drying, concentrating, separating and purifying to obtain the selenium-containing isochroman compound. The synthesis method disclosed by the invention is relatively easy to operate, mild in reaction condition, relatively high in yield, environment-friendly and suitable for large-scale industrial production.

Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water

Phosphine-mediated reductions of substituted propynoic esters and amides in the presence of water yield the partially reduced α,β-unsaturated esters and amides with highZ-selectivity. The competitivein situ ZtoE-isomerization of the product in some cases lowers theZtoEratios of the isolated α,β-unsaturated carbonyl products. Reaction time and the amounts of phosphine and water in the reaction mixture are the key experimental factors which control the selectivity by preventing or reducing the rates ofZ- toE-product isomerization. Close reaction monitoring enables isolation of theZ-alkenes with high selectivities. The computational results suggest that the reactions could be highlyZ-selective owing to the stereoselective formation of theE-P-hydroxyphosphorane intermediate.

Hypervalent iodine(iii) induced oxidative olefination of benzylamines using Wittig reagents

We have developed hypervalent iodine(iii) induced oxidative olefination of primary and secondary benzylamines using 2C-Wittig reagents, which provides easy access to α,β-unsaturated esters. Mild reaction conditions, good to excellent yields with high (E) selectivity, and a broad substrate scope are the key features of this reaction. We have successfully carried out the gram-scale synthesis of α,β-unsaturated esters.